Amido naphthol ethers



Patented Dec. 2, 1947 UNITED STATES PATENT OFFICE AMIDO NAPHTHOL ETHERS Elkan R. Blout, Cambridge, and Richard S. Corley, Boston,

Delaware Mass, assignors to Polaroid Corporation, Cambridge, Mass.,

a corporation of No Drawing. Application September 9, 1946, Serial No. 695,824

N -acetyl-O-methyl-l (2 -naphthylaminomethyl) -2-naphthol represented above, as a pure com pound may take the form of small colorless blocks exhibiting a melting point of about 129-130 C. The compound is soluble in cold pyridine and hot n-butanol, moderately soluble in hot acetone and slightly soluble in benzene and in ethanol. The new compound is insoluble in water and insoluble in cold dilute alcoholic alkali.

N-acetyl-O-methyl- 1 (2' -naphthylaminomethyl) -2-naphthol may be prepared by the aoetylation of O-methyl-l-(2'-naphthylaminomethyl)- 2-naphtho1with acetic anhydride in acetone solution. O-methyl-l- (2' -naphthylaminomethyl) -2- naphthol is disclosed and claimed in copending application Serial No. 695,823 filed on even date herewith.

EXAMPLE 1 N-acetyl-O-methyl- 1- (2' -naphthylaminomethyl) -2-na-phthol may be prepared as follows:

To 3.40 grams of O-methyl-1-(2'-naphthylaminomethyl) -2-naphthol in cc. of hot acetone were added 1.3 cc. of acetic anhydride (1 molar equivalent), The solution was permitted to boil down nearly to dryness. The residue upon crystallization from n-butanol produced 3.50 grams of N acetyl O methyl-1-(2-naphthylaminomethyl) -2-naphthol which exhibited a melting point of about 128-l29 C. For purposes of analysis N-acetyl-O-methyl-l-(2-naphthylaminomethyl) -2-naphthol was crystallized five times from n-butanol and dried in vacuo at about 80 C. The product was pure N-acetyl-O-methyl-l- (2-naphthylaminomethyl)-2-naphthol in the form of small colorless blocks. For determination of the melting point the sample was heated at a rate of 1 C. per 20 seconds. Under these conditions the compound exhibited a melting point of about l29-130 C.

The pure N-acetyl-O-methyl-l-(2-naphthylaminomethyl) -2-naphtho1 which has the empirical formula C24H21NO2 showed by microanalysis the presence of 81.00% carbon and 6.36% hydrogen as compared with the calculated values of 81.12% carbon and 5.96% hydrogen,

Preparation of O-methyZ-I-(2'-naphthylaminomethyl) -2-naphthol Z-methoxy-l-naphthaldehyde was prepared according to the method of Barger and Starling, J. Chem $00., 99, 2301 (1911). To a solution of 4.20 grams of Z-methoxyl-naphthaldehyde in 20 cc. of hot methanol were added 3.20 grams of beta-naphthylamine in 20 cc. of methanol, and the mixture was boiled gently for 15 minutes. On cooling there was obtained 6.60 grams of im pure (2-methoxy-l-naphthaldehyde) -beta-naphthylimine. One crystallization from n-butanol gave 5.70 grams of yellow needles of (2-methoxy- 1 naphthaldehyde) -beta-naphthylimine which exhibited a melting point of about 122-123 C. (2-methoxy-l-naphthaldehyde) -beta naphthylimine is disclosed and claimed in copending application Serial No. 695,822 filed on even date herewith.

A solution of 5.00 grams of (2-methoxy-1-naphthaldehyde) -beta-naphthylimine in cc. of ethyl acetate and 1 cc. of acetic acid was hydrogenated at about 45 pounds per square inch pressure and at room temperature with 0.1 gram of Adams platinum oxide catalyst. The reduction was complete in 15 minutes. The catalyst was filtered, care being taken not to permit the catalyst unnecessarily to be exposed to the atmosphere and to dry during this operation in order not adversely to afiect the yield. The solvent was removed in vacuo at 40 C. to produce a light yellow crystalline residue. The residue was crystallized from ether to give 3.72 grams of nearly colorless needles of O-methyl-1-(2'-naphthylaminomethyl) -2-naphtho1 exhibiting a melting 3 point of about 111-112 C. O-methyl-1-(2'- naphthylaminomethyl)-2-naphtho1 is disclosed and claimed in copending application Serial No. 695,823 filed on even date herewith.

Since certain changes may be made in the above subject matter without departing from the scope of the invention herein involved, it is intended that all matter contained in the above description shall be interpreted as illustrative and not in a limiting sense.

It is also to be understood that the following claim is intended to cover all of the generic and specific features of the invention herein described, and all statements of the scope of the invention which, as a, matter of language, might be said to 5 fall therebetween.

formula:

@ (IIOCH:

' CHzN O CH:

and which in the form of small colorless blocks exhibits a melting point of about 129-130 C.

ELKAN R. BLOUT. RICHARD S. CORLEY. 

